Approximately one-third of countries in the world are regarded as small states. There are also subnational jurisdictions, or small territories, that share similar characteristics of small states. Their small size renders them vulnerable to changes in the global economy, and this, in turn, has an impact on trade, business, and employment. In this paper, we review the characteristics of small states and territories with reference to Macao and the influences on people’s career development. Career paths in small states and territories tend to be characterised by the need for greater flexibility and readiness for adaptation. For this reason, career development practitioners in those settings are recommended to embed the notion of career adaptability within the services and training they provide.